Preparation of 6-Monohalo-β-cyclodextrin Derivatives with Selectively Methylated Rims via Diazonium Salts

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F23%3A10467000" target="_blank" >RIV/00216208:11310/23:10467000 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=q50cH9eEFJ" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=q50cH9eEFJ</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acsomega.3c01950" target="_blank" >10.1021/acsomega.3c01950</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Preparation of 6-Monohalo-β-cyclodextrin Derivatives with Selectively Methylated Rims via Diazonium Salts

Popis výsledku v původním jazyce

A series of 6-monohalo (Cl, Br, and I) β-cyclodextrinderivativeswith various types of methylations were synthesized via a diazotization/nucleophilicdisplacement reaction from the corresponding methylated cyclodextrinamines. All four starting compounds (6(A)-amino-6(A)-deoxy derivatives of native β-CD, per-6-O-methyl-, per-2,3-O-methyl-, and per-2,3,6-O-methyl-β-CD) were found to have different reactivitiesunder the same reaction conditions. Unsubstituted and fully per-O-methylatedcyclodextrin amines undergo fast transformation, giving lower yieldsof the monohalogenated product. The selectively methylated cyclodextrinamines react remarkably slower and provide almost complete conversioninto the desired monohalogenated compound. A pure product was, inseveral cases, successfully isolated with simple purification techniques(extraction and precipitation), allowing large-scale preparations.This new method opens the way for preparing poorly investigated monofunctionalizedselectively methylated cyclodextrins.

Název v anglickém jazyce

Preparation of 6-Monohalo-β-cyclodextrin Derivatives with Selectively Methylated Rims via Diazonium Salts

Popis výsledku anglicky

A series of 6-monohalo (Cl, Br, and I) β-cyclodextrinderivativeswith various types of methylations were synthesized via a diazotization/nucleophilicdisplacement reaction from the corresponding methylated cyclodextrinamines. All four starting compounds (6(A)-amino-6(A)-deoxy derivatives of native β-CD, per-6-O-methyl-, per-2,3-O-methyl-, and per-2,3,6-O-methyl-β-CD) were found to have different reactivitiesunder the same reaction conditions. Unsubstituted and fully per-O-methylatedcyclodextrin amines undergo fast transformation, giving lower yieldsof the monohalogenated product. The selectively methylated cyclodextrinamines react remarkably slower and provide almost complete conversioninto the desired monohalogenated compound. A pure product was, inseveral cases, successfully isolated with simple purification techniques(extraction and precipitation), allowing large-scale preparations.This new method opens the way for preparing poorly investigated monofunctionalizedselectively methylated cyclodextrins.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ACS Omega

ISSN

2470-1343

e-ISSN

2470-1343

Svazek periodika

8

Číslo periodika v rámci svazku

31

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

9

Strana od-do

28268-28276

Kód UT WoS článku

001034638100001

EID výsledku v databázi Scopus

2-s2.0-85167928113